2,5-Dimethoxy-zimtsaeure-aethylester | 15804-86-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 2,5-Dimethoxy-zimtsaeure-aethylester
• 英文别名: Ethyl 3-(2,5-dimethoxyphenyl)prop-2-enoate
• CAS: 15804-86-1
• 化学式: C₁₃H₁₆O₄
• 分子量: 236.268
• InChiKey: XIEVTAMMUAMFIQ-UHFFFAOYSA-N

物化性质

• 沸点：
  359.1±27.0 °C(Predicted)
• 密度：
  1.099±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,5-Dimethoxy-zimtsaeure-aethylester 在 tetraphosphorus decasulfide 作用下， 以 1,4-二氧六环 为溶剂， 以78%的产率得到ethyl 2',5'-dimethoxythionocinnamate
  参考文献：
  名称：

  Novel natural product-based cinnamates and their thio and thiono analogs as potent inhibitors of cell adhesion molecules on human endothelial cells

  摘要：

  In the present study, we report the design and synthesis of novel analogs of cinnamates, thiocinnamates and thionocinnamates and evaluated the potencies of these analogs to inhibit TNF-alpha induced ICAM-1 expression on human endothelial cells. By using whole cell-ELISA, our screening data demonstrated that ethyl 3',4',5'-trimethoxythionocinnamate (ETMTC) is the most potent inhibitor of TNF-alpha induced ICAM-1, VCAM-1 and E-selectin. As functional consequences, ETMTC abrogated TNF-alpha induced adhesion of neutrophils to the endothelial monolayer. Structure activity relationship studies revealed the critical role of the chain-length of the alkyl group in the alcohol moiety, number of methoxy groups in the aromatic ring of the cinnamoyl moiety and the presence of the alpha, beta- C-C double bond in the thiocinnamates and thionocinnamates. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.09.008
• 作为产物：
  描述：

  2,5-二甲氧基苯甲醛 在 盐酸 、 sodium acetate 作用下， 生成 2,5-Dimethoxy-zimtsaeure-aethylester
  参考文献：
  名称：

  New parliament, new politics in Scotland

  摘要：

  DOI：

  10.1093/pa/53.3.605

文献信息

• Synthesis of C4C5 Cycloalkyl-Fused and C6-Modified Chromans via<i>ortho</i>-Quinone Methides
  作者：Kassrin Tangdenpaisal、Kanokpish Chuayboonsong、Patchaya Sukjarean、Varisa Katesampao、Nok Noiphrom、Somsak Ruchirawat、Poonsakdi Ploypradith

  DOI：10.1002/asia.201403356

  日期：2015.4

  from 3,5‐dimethoxybenzaldehyde, some functionalized 2,3,4‐trisubstituted tricyclic 4,5‐cycloalkyl‐fused and 6‐modified chromans could be prepared via ortho‐quinone methides (o‐QMs)/hetero‐Diels–Alder (HDA) reactions of the appropriate precursors. The bromide at C6 served as a handle for introducing other substituents through palladium‐catalyzed cross‐coupling reactions and other functional‐group transformations

  从3,5-二甲氧基苯甲醛开始，可以通过邻醌甲基（o -QMs）/杂Diels-Alder（ HDA）适当前体的反应。C6处的溴化物可作为通过钯催化的交叉偶联反应和其他官能团转化引入其他取代基的方法。在[PtCl 4 ]催化下可获得中等至高产率（高达80％）和非对映选择性（高达> 99：1）。优选内切环加成反应中的过渡态中管理在C2的立体化学结果起到了重要作用 C3 C4。在构型上固定Ë双环的几何ö -QMs影响了环加成反应，以有利于C2  C4顺式关系。
• Controlling reactivity in the Fujiwara–Moritani reaction: Examining solvent effects and the addition of 1,3-dicarbonyl ligands on the oxidative coupling of electron rich arenes and acrylates
  作者：Roderick C. Jones

  DOI：10.1016/j.tetlet.2019.151471

  日期：2020.2

  alkenation of electron rich arenes in the presence of K2S2O8 with an acetic acid/1,4-dioxane solvent combination has been developed. The 1,4-dioxane co-solvent dramatically influences the rate of reaction, giving selectively disubstituted alkenes, while the addition of acetylacetone ligands was shown to increase site selectivity for the alkenation of monofunctionalized arenes. The participation of these

  已经开发了在K 2 S 2 O 8存在下，用乙酸/ 1,4-二恶烷溶剂组合的钯催化的富电子芳烃的直接烷化反应。1,4-二恶烷共溶剂显着影响反应速率，产生选择性二取代的烯烃，而乙酰丙酮配体的添加显示出增加了单官能化芳烃链烯化的位点选择性。这些羰基配体的参与已通过ESI-MS研究确认，并确定了催化循环中的一些关键原位中间体。可以在直接氧化偶合中使用多种富电子芳烃和烯烃底物，以中等至良好的产率得到二取代的烯烃。
• Organocatalytic enantioselective formal synthesis of HRV 3C-protease inhibitor (1R,3S)-thysanone
  作者：Rajiv T. Sawant、Suresh B. Waghmode

  DOI：10.1016/j.tet.2008.12.060

  日期：2009.2

  A short and efficient organocatalytic enantioselective formal synthesis of HRV 3C-protease inhibitor (1R,3S)-thysanone is achieved in a nine-step with 98.7% enantiomeric excess, by employing L-proline-catalyzed asymmetric of alpha-aminooxylation of aldehyde and Oxa-Pictet-Spengler cyclization as the key steps. (C) 2008 Elsevier Ltd. All rights reserved.